1.	D
[1]

2.	A
[1]

3.	C
[1]

4.	D
[1]

5.	C
[1]

6.	B
[1]

7.	(i)

	curly arrow going from lone pair/negative charge on O in HO– to C;
Do not allow curly arrow originating on H in HO–.
	curly arrow showing Cl leaving;
Accept curly arrow either going from bond between C and Cl to Cl in
2-chloro-3-methylbutane or in the transition state.
	representation of transition state showing negative charge, square
brackets and partial bonds;
Do not penalize if HO and Cl are not at 180° to each other.
Do not award M3 if OH ---- C bond is represented.
	formation of organic product 3-methylbutan-2-ol and Cl–;	4

(ii)	OH– has a negative charge/higher electron density;
greater attraction to the carbon atom (with the partial positive
charge) / OWTTE;	2
Do not allow just greater attraction.
[6]

8.	(a)	A: l-bromobutane;
B: 2-bromobutane;
C: 2-bromo-2-methylpropane;
D: 1-bromo-2-methylpropane;
Penalize incorrect punctuation, e.g. commas for hyphens, only once.
Accept 2-bromomethylpropane and 1-bromomethylpropane for
C and D respectively.	4
 
(b)	(i)	C/2-bromo-2-methylpropane;
unimolecular nucleophilic substitution;	2
 
(ii)	RBr → R+ + Br–;
Allow use of 2-bromo-2-methylpropane instead of RBr.	1
 
(iii)	A/1-bromobutane/D/1-bromo-2-methylpropane;

	curly arrow going from lone pair/negative charge on O in OH– to C;
Do not allow curly arrow originating on H in OH–.
	curly arrow showing Br leaving;
Accept curly arrow either going from bond between C and Br to Br in
1-bromobutane or in the transition state.
	representation of transition state showing negative charge, square
brackets and partial bonds;
Do not penalize if HO and Br are not at 180° to each other.
Do not award fourth mark if OH----C bond is represented.	4

(c)	(b)(i) no change as [OH–] does not appear in rate equation/in
the rate determining step;
(b) (iii) rate doubles as the rate is proportional to [OH–] / OH–
appears in the rate-determining/slow step / first order with
respect to OH–;
Award [1] if correctly predicts no rate change for SN1 and
doubling of rate for SN2 of without suitable explanation.	2
 
(d)	rate of 1-bromobutane is faster;
C–Br bond is weaker/breaks more easily than C–Cl bond;	2
 
(e)	2-bromobutane/B;
(plane-) polarized light shone through;
enantiomers rotate plane of plane-polarized light to left or right/
opposite directions (by same amount);
Accept “turn” instead of “rotate” but not “bend/reflect”.
	physical properties identical (apart from effect on plane-polarized light);
chemical properties are identical (except with other chiral compounds);
Do not accept “similar” in place of “identical”.	5
 
(f)	(i)	elimination;	1

(ii)

	curly arrow going from lone pair/negative charge on O in OH– to H on β-C;
Do not allow curly arrow originating on H in OH–.
Allow C2H5O– instead of OH–.
	curly arrow going from CH bond to form C=C bond;
curly arrow showing Br leaving;
	Accept the following for first 3 marks.

	curly arrow showing Br leaving;
representation of carbocation;
curly arrow going from lone pair/negative charge on O in OH–
to H on C adjacent to C+ and curly arrow going from
CH bond to form C=C bond;
	two products formed: but-1-ene / but-2-ene/(cis) but-2-ene/
(trans) but-2-ene;
Award [1] for two correct answers.	4 max
[25]

9.	(i)	SN2;	1
 
(ii)

curly arrow going from CN– to C;
curly arrow showing Br leaving;
Curly arrow may be represented on transition state.
	representation of transition state, showing negative charge and dotted lines;
products;	4
 
(iii)	CH3CH2CN + 2H2 → CH3CH2CH2NH2;
Ni / Pt / Pd;	2
[6]

10.	(i)	CH3CH2Br + OH– → CH3CH2OH + Br–;
CH3CH2Br + OH– → CH2=CH2 + H2O + Br–;
Accept KOH and KBr in the balanced equations
	dilute KOH compared to concentrated KOH;
aqueous KOH compared to ethanolic KOH;
warm/40–50 °C compared to hot/80-100 °C;
Accept any two reaction conditions.	4 max
 
(ii)

curly arrow from O to H;
curly arrow from C–H to C–C;
curly arrow showing Br leaving;
products CH2=CH2 + Br– + C2H5OH/H2O;	4
 
(iii)	addition;	1
[9]

11.	(i)	hot;
alcoholic OH– /NaOH/KOH;
C2H5Br + C2H5ONa → C2H4 + NaBr + C2H5OH /
C2H5Br + NaOH → C2H4 + NaBr + H2O;
Accept ionic equation with C2H5O– or OH–.	3
 
(ii)	OH– reacts with ethanol to form ethoxide ion/C2H5OH + OH– → C2H5O– + H2O;

curly arrow going from lone pair/negative charge on O in C2H5O– /CH3CH2O– to
H on β–C;
Accept arrow origin from OH– but do not allow curly arrow
originating on H in OH–.
Accept OH– in place of C2H5O–(to form H2O).
	curly arrow going from CH bond to form C=C bond;
curly arrow showing Br leaving;
structural formula of organic product CH2=CH2;
	Award [4 max] for E1 mechanism (unstable primary carbocation)

curly arrow showing Br leaving;
representation of primary carbocation;
curly arrow going from lone pair on O in H2O to H on C
adjacent to C+ and curly arrow going from CH bond to
form C=C bond;
structural formula of organic product CH2=CH2;	5
[8]

12.	B
[1]

13.	B
[1]

14.	D
[1]

15.	(i)

Accept CH3CH2CH2Br.	Accept CH3CH2CH2CH2NH2.
Penalize missing H atoms.		1
 
(ii)	CH3CH2CH2Br + KCN → CH3CH2CH2CN + KBr;
Accept ionic equation.
	CH3CH2CH2CN + 2H2 → CH3CH2CH2CH2NH2;
Equation must be balanced for mark.
Accept LiAlH4 in place of reaction with hydrogen.
	For the second equation:
Ni (as catalyst);
heat/150 °C;	4
[5]

16.	D
[1]

17.	B
[1]

18.	B
[1]

19.	(i)	compounds with the same (molecular formula and) structural formula but
different arrangements of atoms in space / OWTTE;	1
 
(ii)

Allow [1 max] if structures are correct but arrangement of groups in space
does not clearly show the cis/ trans isomerism.

(iii)

Allow [1 max] if the structures are correct but it is not clear that they are
mirror images.	2
[3]